(S)-2-chlorocarbonyl-pyrrolidine-1-carboxylic acid tert-butyl ester → (S)-2-(5,6,7,8-tetrahydro-1H-pyrrolo[3,2-b]azepine-4-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1839662ノート

反応式

HRID 1839662 の反応式
[NH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:4]=2[CH:3]=[CH:2]1.[C:11]([O:15][C:16]([N:18]1[CH2:22][CH2:21][CH2:20][C@H:19]1[C:23](Cl)=[O:24])=[O:17])([CH3:14])([CH3:13])[CH3:12]>C(Cl)Cl>[C:11]([O:15][C:16]([N:18]1[CH2:22][CH2:21][CH2:20][C@H:19]1[C:23]([N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[NH:1][CH:2]=[CH:3][C:4]1=2)=[O:24])=[O:17])([CH3:14])([CH3:13])[CH3:12]

参加物

4

反応物 2

HCID 11148997(S)-2-chlorocarbonyl-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 225617901,4,5,6,7,8-Hexahydropyrrolo[3,2-B]azepine

生成物 1

HCID 20761536(S)-2-(5,6,7,8-tetrahydro-1H-pyrrolo[3,2-b]azepine-4-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (S)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (664 mg) in DCM (10 mL) at 0° C. was added oxalyl chloride (4.7 mmol), followed by one drop of DMF. After stirring at rt for 2 hours, the solvent was concentrated to give S)-2-chlorocarbonyl-pyrrolidine-1-carboxylic acid tert-butyl ester. To a solution of 1,4,5,6,7,8-hexahydro-pyrrolo[3,2-b]azepine (350 mg, 2.6 mmol) was added TEA (362μL) and (S)-2-chlorocarbonyl-pyrrolidine-1-carboxylic acid tert-butyl ester (dissolved in 10 mL of DCM). After stirring at rt for overnight, the reaction was diluted with DCM, washed with NaHCO3, brine, dried and concentrated. The residue was purified on a silica gel column to give 410 mg of (S)-2-(5,6,7,8-tetrahydro-1H-pyrrolo[3,2-b]azepine-4-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as a light brown liquid.

後処理

  1. washwashed with NaHCO3, brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified on a silica gel column

出典と根拠

ORDレコード
ord-36d73ea88af54453b60d369c13af4b4d
出典データセット
uspto-grants-2004_01
特許番号
US06677368B2

反応ノート

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